Water → HCID 54473444, compound

HRID 2379862Notes

Reaction equation

HRID 2379862 reaction equation
Cl.Cl.Cl.[NH2:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]2[N:13]=[C:14]([N:17]=[C:18]([NH2:20])[NH2:19])[S:15][CH:16]=2)[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[CH3:28][O:29][CH2:30][C:31](Cl)=[O:32].O>CN(C)C=O>[NH2:19][C:18](=[N:17][C:14]1[S:15][CH:16]=[C:12]([C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:5][NH:4][C:31](=[O:32])[CH2:30][O:29][CH3:28])[N:11]=2)[N:13]=1)[NH2:20]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 189538374-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride

Product 1

HCID 54473444HCID 54473444, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride (3.0 g) and triethylamine (4.7 ml) in N,N-dimethylformamide (60 ml) was added a methoxyacetyl chloride (0.9 ml) under ice-cooling and the mixture was stirred for 2.5 hours at the same temperature. The reaction mixture was added to water and the mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of methanol, dioxane and diisopropyl ether to give 2-(diaminomethyleneamino)-4-(6-methoxyacetylaminomethylpyridin-2-yl)thiazole (0.86 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran
  3. washThe extract layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from a mixture of methanol, dioxane and diisopropyl ether

Sources & evidence

ORD record
ord-b5109e84843245d1bfc761efd71630f7
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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